Stadium: Cancha 1 Round: 24 Ground: Hardcourt outdoor
| Challenger Drummondville | 2019/03/11 18:45 | Michael Redlicki v Roy Smith | 6-1,6-1 |
| Challenger Yokohama | 2019/02/25 02:30 | Kaichi Uchida v Roy Smith | 6-3,6-3 |
| ATP New York | 2019/02/10 21:20 | Ramkumar Ramanathan v Roy Smith | 4-6,6-2,6-4 |
| Challenger Cleveland | 2019/01/30 02:55 | Roy Smith v Donald Young | 6-4,0-6,7-6 |
| Challenger Cleveland | 2019/01/28 18:25 | Roy Smith v Gijs Brouwer | 7-6,6-3 |
| Challenger Newport Beach | 2019/01/21 19:30 | Roy Smith v Benjamin Bonzi | 2-6,5-7 |
| Challenger Canberra | 2019/01/07 04:15 | Tomas Barrios Vera v Roy Smith | 7-6,6-3 |
| Challenger Noumea | 2018/12/31 06:15 | Marc-Andrea Huesler v Roy Smith | 6-4,7-6 |
| ATP Miami | 2019/03/22 22:45 | Roberto Bautista-Agut v Janko Tipsarevic | 7-6,6-4 |
| ATP Miami | 2019/03/20 18:50 | Janko Tipsarevic v Bradley Klahn | 6-3,6-3 |
| Challenger Bangkok | 2019/02/14 06:15 | James Duckworth v Janko Tipsarevic | 4-6,6-3,6-2 |
| Challenger Bangkok | 2019/02/13 04:50 | Janko Tipsarevic v Marc Polmans | 6-2,3-6,6-3 |
| Challenger Bangkok | 2019/02/12 04:10 | Tsung-Hua Yang v Janko Tipsarevic | 2-6,6-4,4-6 |
| Australian Open | 2019/01/14 01:35 | Grigor Dimitrov v Janko Tipsarevic | 4-6,6-3,6-1,6-4 |
| Kooyong Classic | 2019/01/08 02:35 | Jason Kubler v Janko Tipsarevic | 4-6,6-3,10-12 |
| US Open | 2017/08/30 23:05 | Diego Schwartzman v Janko Tipsarevic | 6-2,6-4,7-5 |